Methyl 4-bromo-2-chloronicotinate

Name: Methyl 4-bromo-2-chloronicotinate
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CAS No. 1064678-14-3
Cat. No. CS-0112315
Purity≥98%
MDL No.MFCD21364445

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FedEx Limited Quantities Ground	$0.00
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Methyl 4-bromo-2-chloronicotinate|CS-0112315

Structure of 1064678-14-3

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General Information

CAS No. 1064678-14-3
Cat. No. CS-0112315
Purity ≥98%
MDL No. MFCD21364445
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₅BrClNO₂
Molecular Weight 250.48
Synonym(s) methyl 4-bromo-2-methylnicotinate
SMILES O=C(C1=C(Br)C=CN=C1Cl)OC

Description

Methyl 4-bromo-2-chloronicotinate features a uniquely activated pyridine core bearing bromo and chloro substituents at the 4- and 2-positions, respectively. This electron-deficient heterocycle enables efficient cross-coupling reactions under palladium catalysis. The methyl ester group provides stability and facilitates downstream derivatization. This compound serves as a key intermediate in the synthesis of bioactive nitrogen-containing scaffolds.

Application

Methyl 4-bromo-2-chloronicotinate serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its complementary halogenation pattern. The bromo and chloro substituents facilitate sequential functionalization under orthogonal conditions, while the methyl ester group supports subsequent transformations such as hydrolysis or reduction. Its bench-stable nature and compatibility with standard synthetic workflows make it ideal for constructing complex scaffolds in medicinal chemistry and agrochemical research.

Synthesis

Route1
- In-stock
  
  73583-37-6
- 79-22-1
- ~96%
- In-stock
  
  1064678-14-3
References
- Gibson, Christoph; Schnatbaum, Karsten; Pfeifer, Jochen R.; Locardi, Elsa; Paschke, Matthias; Reimer, Ulf; Richter, Uwe; Scharn, Dirk; Faussner, Alexander; Tradler, Thomas Journal of Medicinal Chemistry, 2009 , vol. 52, # 14 p. 4370 - 4379

Safety Information

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GHS Pictogram :	GHS No : GHS08,GHS09
Signal Word : Danger	UN#: 3077
Class : 9	Packing Group : Ⅲ
Hazard Statements : H302-H361-H372-H410
Precautionary Statements : P264-P280-P301+P330+P331

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Computational Chemistry Data

TPSA 39.19
LogP 2.2841
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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Methyl 4-bromo-2-chloronicotinate

CAS No. 1064678-14-3

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